Phosphorus sulfide (P2S5) → HCID 178448735, compound

HRID 1726929Notes

Reaction equation

HRID 1726929 reaction equation
[CH2:1]([N:5]1[C:10](=O)[CH2:9][NH:8][C:7]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([Cl:19])[CH:13]=2)=[N:6]1)[CH2:2][CH2:3][CH3:4].P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:21]>C1(C)C=CC=CC=1>[CH2:1]([N:5]1[C:10](=[S:21])[CH2:9][NH:8][C:7]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([Cl:19])[CH:13]=2)=[N:6]1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 14817Phosphorus sulfide (P2S5)HCID 178448734HCID 178448734, compound

Product 1

HCID 178448735HCID 178448735, compoundYield 68.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
95 °C

Procedure

To a solution of 1.31 grams of 1-butyl-3-(3,4-dichlorophenyl)-4,5-dihydro-1,2,4-triazin-6-one (4.4 mmol) in 12 mL of toluene was added 0.37 gram of phosphorus pentasulfide (8.3 mmol). The reaction was heated to 95° C. for seven hours. After cooling 1.4 grams of flash grade silica gel was added. The reaction was filtered through Celite and concentrated under reduced pressure. The oil was chromatographed with 22% ethyl acetate/hexanes and 0.95 grams of 1-butyl-3-(3,4-dichlorophenyl)-4,5-dihydro-1,2,4-triazin-6-thione was isolated.

Workup

  1. temperatureAfter cooling 1.4 grams of flash grade silica gel
  2. additionwas added
  3. filtrationThe reaction was filtered through Celite
  4. concentrationconcentrated under reduced pressure
  5. customThe oil was chromatographed with 22% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-612ed9a6a926492b8f9278c76c2535c9
Source dataset
uspto-grants-2009_02
Patent number
US07494996B2

Reaction notes

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